TY - JOUR A1 - Adorjan, I. A1 - Rosenau, Th. A1 - Potthast, A. A1 - Kosma, P. A1 - Mereiter, K. A1 - Pauli, Jutta A1 - Jäger, Christian T1 - Crystal and molecular structure of methyl 4-O-methyl-beta-D-ribo-hex-3-ulopyranoside JF - Carbohydrate research N2 - Methyl 4-O-methyl-?-Image-ribo-hex-3-ulopyranoside (2), a model compound for partially oxidized anhydroglucose units in cellulose, was crystallized from CHCl3/n-hexane by vapor diffusion to give colorless plates. Crystal structure determination revealed the monoclinic space group P21 with Z=2C8H14O6 and unit cell parameters of a=8.404(2), b=4.5716(10), c=13.916(3) Å, and ?=107.467(4)°. The structure was solved by direct methods and refined to R=0.0476 for 1655 reflections and 135 parameters. The hexulopyranoside occurs in a distorted chair conformation. Both hydroxyls are involved in hydrogen bonding and form zigzag bond chains along the b-axis. One of the two hydrogen bonds is bifurcated. The solid-state 13C NMR spectrum of 2 exhibits eight carbon resonances, with well-separated signals for the two methoxyls (1-OMe: 55.72 ppm, 4-OMe: 61.25 ppm) and a keto resonance with relatively large downfield shift (206.90 ppm). Differences in the C-4 and the methoxyls’ chemical shifts in the solid and liquid states were found KW - Crystal structure KW - Solid-state NMR KW - Cellulose KW - Carbonyl groups PY - 2004 DO - https://doi.org/10.1016/j.carres.2004.01.006 SN - 0008-6215 SN - 1873-426X VL - 339 IS - 4 SP - 795 EP - 799 PB - Elsevier CY - Amsterdam AN - OPUS4-5341 LA - eng AD - Bundesanstalt fuer Materialforschung und -pruefung (BAM), Berlin, Germany ER -